A selective, practical and general incorporation of fluoroalkyl groups into organic frameworks is of great interest for synthesis. Herein we report the first metal-free, initiator-free, and general photochemical perfluoroalkylation of a variety of N,N-dialkylhydrazones at room temperature in the absence of any external photocatalyst. It constitutes an important advance in perfluoroalkyl radical addition to CN π bonds for the synthesis of hydrazones instead of amines. Affordable and easily available perfluoroalkyl iodides serve as effective precursors. The excellent regio-, stereo- and chemoselectivity as well as the broad substrate scope make this a very promising synthetic tool.
- This article is part of the themed collections: HOT articles in Organic Chemistry Frontiers in 2016 and Celebrating the 75th Birthday of Professor Barry Trost